N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide

Base Information

Chemical Name:N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide
CAS No.:1415209-01-6
Molecular Formula:C₁₈H₁₆BrFN₄O₂S
Molecular Weight:451.319
Hs Code.:

Synonyms:N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide

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Chemical Property of N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide

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Technology Process of N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide

There total 5 articles about N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1415209-02-7
tert-butyl (4aR,7aR)-7a-(5-(5-bromopicolinamido)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

: 1415209-01-6
N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide

Guidance literature:: tert-butyl (4aR,7aR)-7a-(5-(5-bromopicolinamido)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

With ammonium hydroxide; In methanol; dichloromethane;

Reference yield:

: (+/-)-tert-butyl (4aR,7aR)-7a-(5-(5-bromopicolinamido)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate

: 1415209-01-6
N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide

Guidance literature:: Multi-step reaction with 2 steps

1: chiralcel OD / diethylamine; n-heptane; ethanol

2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With trifluoroacetic acid; In ethanol; n-heptane; dichloromethane; diethylamine;

Reference yield:

: 1415208-88-6
tert-butyl ((4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate

: 1415209-01-6
N-(3-((4aR,7aR)-2-amino-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-bromopicolinamide

Guidance literature:: Multi-step reaction with 4 steps

1: (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate / 80 °C

2: palladium on activated charcoal; hydrogen / methanol

3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine

4: trifluoroacetic acid

With sodium azide; copper(ll) sulfate pentahydrate; palladium on activated charcoal; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; hydrogen; benzotriazol-1-ol; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol;
DOI:10.1016/j.bmcl.2016.10.055